US10603329B2 - Phospholipid complexes of curcumin having improved bioavailability - Google Patents
Phospholipid complexes of curcumin having improved bioavailability Download PDFInfo
- Publication number
- US10603329B2 US10603329B2 US12/281,994 US28199407A US10603329B2 US 10603329 B2 US10603329 B2 US 10603329B2 US 28199407 A US28199407 A US 28199407A US 10603329 B2 US10603329 B2 US 10603329B2
- Authority
- US
- United States
- Prior art keywords
- curcumin
- complex
- phospholipid
- extract
- phospholipids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active, expires
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
- A61K47/544—Phospholipids
Definitions
- the present invention relates to novel phospholipids complexes of curcumin or extracts containing it having improved bioavailability.
- Curcumin [1,7-bis(4-hydroxyl-3-methoxyphenyl)-1,6-heptadiene-3,5-dione], is the major constituent of the spice turmeric extracted from the root of Curcuma longa Linn.
- Curcumin is a polyphenol that has powerful antioxidant and inhibits the expression of the enzyme cyclooxygenase 2 (Cox 2) at least in part via interference with activation of the transcription factor NFkB [2, 14].
- Cox 2 cyclooxygenase 2
- curcumin inhibits the growth of cancer cells with an IC 50 value of 20-75 ⁇ M [6, 16].
- curcumin has been shown to prevent cancer in the colon, skin, stomach, duodenum, soft palate, tongue, sebaceous glands and breast [9, 10, 15].
- curcumin could be considered a promising efficacious and safe cancer chemopreventive agents [18].
- clinical pilot studies have associated curcumin consumption with regression of pre-malignant lesions of bladder, soft palate stomach, cervix and skin [1, 11].
- Complex compounds of vegetable extracts or of purified components thereof with natural, synthetic or semi-synthetic phospholipids have been disclosed, e.g., in EP 209 038, EP 275 005, EP 283 713, EP 1 035 859 and EP 1 140 115. Said complexes improve the plasma bioavailability of the extract or purified component, thanks to their lipophilicity.
- EP 1 140 115 generically mentions ethanol among the various solvents that can be used of the preparation of said complexes, but does not provide preparation examples which make use of ethanol as the solvent.
- the complexes disclosed are phospholipid complexes of proanthocyanidin A2, which are quite different in the chemical structure with respect to the phospholipids complexes of curcumin of the present invention.
- the present invention relates to novel phospholipids complexes of curcumin having improved bioavailability.
- phospholipids of either vegetable or synthetic origin can be used, particularly preferred are soy phospholipids, such as phosphatidyl choline, phosphatidyl serine, phosphatidyl ethanolamine.
- the complexes are prepared by adding the phospholipid to curcumin dissolved in a protic solvent, more particularly adding the phospholipid to the ethanol solution of the hydroalcoholic extract of turmeric rhizomes, under reflux and with stirring.
- the resulting suspension is concentrated under reduced pressure to a residue which is dried in oven.
- the ratio of phospholipids to curcumin is in the range from 10 to 1 w/w, a more preferable mole ratio being 5:1 w/w.
- the present invention also relates to pharmaceutical compositions containing as the active principle one of the phospholipids complexes of curcumin according to the invention, in admixture with a suitable pharmaceutical carrier.
- the present invention further relates to the use of the phospholipids complexes of curcumin of the invention for the preparation of medicaments having chemopreventive action.
- Ground dry turmeric rhizomes 1000 g were extracted with ethanol-water 9:1 mixture (6680 ml). The resulting hydroalcoholic solution was concentrated under reduced pressure and drying was completed in oven at 60° C. under vacuum to yield 69.3 g of an orange paste having a curcumin content of 17.4% w/w and a total curcuminoid content of 29.2% w/w.
- Ground dry turmeric rhizomes 1000 g were defatted with hexane (2500 ml) before being extracted with ethanol-water 95:5 mixture (7500 ml). Curcuminoids were then crystallized by slowly adding hexane (500 ml) to the hydroalcoholic solution and allowing the resulting mixture to stand for 24 hours. A microcrystalline orange solid was filtered and dried at 60° C. under vacuum to yield 36.7 g of extract having a curcumin content of 71.74% and a total curcuminoid content of 93.8% w/w.
- the 1 H-NMR spectrum of the complex in CDCl 3 shows the main signals of the phospholipids, typical of complexed phospholipids.
- the 1 H-NMR spectrum of the complex in DMSO-d 6 which is a solvent preventing the aggregation of the complex, shows the signals of the free starting extract as well as those of the phospholipids.
- the signal of 31 P in CDCl 3 is at 1.06 ppm and is 35.3 Hz wide, which is typical of complexed phospholipids.
- the complex is destroyed in DMSO-d 6 as confirmed by the signal of 31 P at 0.12 ppm with 3.80 Hz width typical of the free phospholipid.
- Tests were carried out to compare curcumin bioavailability afforded by the phospholipid complexes of the invention and by the extract containing uncomplexed curcumin.
- Rats were killed at 15, 30, 60 and 120 min. Whole blood was collected into heparinized tubes, centrifuged immediately at 7000 ⁇ g for 15 min, plasma was then decanted and stored at ⁇ 80° C. until analysis.
- curcumin and metabolites were verified by negative ion electrospray liquid chromatography/tandem mass spectrometry as previously described (4, 5, 7).
- the improved bioavailability of phospholipid complex of curcumin increases the potential scope of medical applications for curcumin as a chemopreventive agent.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06004820A EP1837030A1 (en) | 2006-03-09 | 2006-03-09 | Phospholipid complexes of curcumin having improved bioavailability |
EP06004820.4 | 2006-03-09 | ||
EP06004820 | 2006-03-09 | ||
PCT/EP2007/001487 WO2007101551A2 (en) | 2006-03-09 | 2007-02-21 | Phospholipid complexes of curcumin having improved bioavailability |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/001487 A-371-Of-International WO2007101551A2 (en) | 2006-03-09 | 2007-02-21 | Phospholipid complexes of curcumin having improved bioavailability |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/274,623 Continuation US20190175628A1 (en) | 2006-03-09 | 2019-02-13 | Phospholipid complexes of curcumin having improved bioavailability |
Publications (2)
Publication Number | Publication Date |
---|---|
US20090131373A1 US20090131373A1 (en) | 2009-05-21 |
US10603329B2 true US10603329B2 (en) | 2020-03-31 |
Family
ID=36677274
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/281,994 Active 2032-08-24 US10603329B2 (en) | 2006-03-09 | 2007-02-21 | Phospholipid complexes of curcumin having improved bioavailability |
US16/274,623 Abandoned US20190175628A1 (en) | 2006-03-09 | 2019-02-13 | Phospholipid complexes of curcumin having improved bioavailability |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/274,623 Abandoned US20190175628A1 (en) | 2006-03-09 | 2019-02-13 | Phospholipid complexes of curcumin having improved bioavailability |
Country Status (17)
Country | Link |
---|---|
US (2) | US10603329B2 (no) |
EP (2) | EP1837030A1 (no) |
JP (1) | JP5448462B2 (no) |
KR (1) | KR101423269B1 (no) |
CN (1) | CN101400360A (no) |
AU (1) | AU2007222667B2 (no) |
CA (1) | CA2644017C (no) |
DK (1) | DK1991244T3 (no) |
ES (1) | ES2757580T3 (no) |
HU (1) | HUE046597T2 (no) |
IL (1) | IL193966A (no) |
NO (1) | NO344242B1 (no) |
PL (1) | PL1991244T3 (no) |
PT (1) | PT1991244T (no) |
RU (1) | RU2450818C2 (no) |
SI (1) | SI1991244T1 (no) |
WO (1) | WO2007101551A2 (no) |
Families Citing this family (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9192644B2 (en) * | 2006-03-06 | 2015-11-24 | The Regents Of The University Of California | Bioavailable curcuminoid formulations for treating Alzheimer's disease and other age-related disorders |
WO2009080850A1 (es) | 2007-12-21 | 2009-07-02 | Asac Compañia De Biotecnologia E Investigacion, S.A. | Método para aumentar la eficacia terapéutica de los curcuminoides y análogos. |
US9700525B2 (en) | 2008-08-20 | 2017-07-11 | Board Of Supervisors Of Louisiana State University And Agricultural & Mechanical College | Continuous local slow-release of therapeutics for head and neck problems and upper aerodigestive disorders |
WO2010023128A1 (en) * | 2008-08-29 | 2010-03-04 | Chr. Hansen A/S | Turmeric curcumin compositions with low residual solvent |
IT1395086B1 (it) * | 2009-03-11 | 2012-09-05 | Velleja Res Srl | Composizioni comprendenti curcumina in forma complessata con fosfolipidi e piperina ad azione chemio-sensibilizzante |
SI2229940T1 (sl) | 2009-03-20 | 2016-01-29 | Bioxtract S.A. | Farmacevtski sestavek s protivnetnimi in antihistaminskimi lastnostmi |
ES2604127T3 (es) | 2009-03-20 | 2017-03-03 | Bioxtract S.A. | Composición farmacéutica que presenta propiedades antiinflamatorias |
IT1395351B1 (it) | 2009-07-09 | 2012-09-14 | Axioma Srl | Formulazioni orali ad elevata biodisponibilita' orale costituite da miscele di frazioni lipofile e idrofile ottenute a partire dalla propoli |
WO2011082290A2 (en) | 2009-12-31 | 2011-07-07 | Organomed Corporation | Formulations from natural products, turmeric, and aspirin |
CN102068419A (zh) * | 2010-12-28 | 2011-05-25 | 神威药业有限公司 | 一种姜黄素组合物 |
US8785380B2 (en) | 2011-02-01 | 2014-07-22 | M/S Akay Flavours & Aromatics Pvt Ltd. | Formulation containing curcuminoids exhibiting enhanced bioavailability |
KR20150064234A (ko) | 2011-05-16 | 2015-06-10 | 옴니액티브 헬스 테크놀로지스 리미티드 | 증가된 생체이용률을 갖는 커큐민을 포함하는 수용성 조성물 및 이의 방법 |
ITTO20110901A1 (it) * | 2011-10-10 | 2013-04-11 | Medestea Biotech S P A | Composizione sinergica per la prevenzione ed il trattamento di disturbi connessi all'invecchiamento |
ITPD20120021A1 (it) * | 2012-01-26 | 2013-07-27 | Fidia Farmaceutici | "nuove composizioni farmaceutiche contenenti fosfatidilserina e curcumina". |
US20150110866A1 (en) * | 2012-05-22 | 2015-04-23 | Harold Gordon Cave | Complexes and compositions containing curcumin |
EP2852395A4 (en) * | 2012-05-22 | 2015-12-16 | Harold Gordon Cave | IMPROVED COMPLEXES AND COMPOSITIONS WITH CURRICULUM |
CN103120798A (zh) * | 2013-01-10 | 2013-05-29 | 施冬云 | 一种具有抗氧化应激作用的磷脂复合物制备方法及其应用 |
US20160000714A1 (en) | 2013-03-06 | 2016-01-07 | Capsugel Belgium Nv | Curcumin solid lipid particles and methods for their preparation and use |
EP2996704B1 (en) * | 2013-05-14 | 2021-01-06 | Mars, Incorporated | Joint care composition |
RU2677894C2 (ru) * | 2014-02-20 | 2019-01-22 | Индена С.П.А. | Композиции, содержащие экстракты Curcuma Longa и Echinacea angustifolia, которые являются полезными для уменьшения периферического воспаления и боли |
RU2571270C1 (ru) * | 2014-07-17 | 2015-12-20 | Открытое Акционерное Общество "Фаберлик" | Липосомальное наносредство на основе продуктов, полученных из корневищ куркумы |
CA2963942A1 (en) * | 2014-10-08 | 2016-04-14 | Boston Biopharm, Inc. | Compositions and methods for increasing the bioavailability of one or more compounds |
EP3218006A4 (en) * | 2014-11-11 | 2018-08-15 | Verdure Sciences | Stable solid lipid particle composition for improved bioavailability of lipophilic compounds for age-related diseases |
WO2016087261A1 (en) | 2014-12-04 | 2016-06-09 | Capsugel Belgium N.V. | Lipid multiparticulate formulations |
EP3150214A1 (en) * | 2015-10-01 | 2017-04-05 | INDENA S.p.A. | Compositions containing extracts of curcuma spp and zingiber officinale which are useful to reduce peripheral inflammation and pain |
WO2017095138A1 (en) * | 2015-11-30 | 2017-06-08 | Gil Medical Center | Curcumin-containing lipid nanoparticle complex comprising ginsenosides |
CN108366974A (zh) * | 2015-12-16 | 2018-08-03 | 维韦克·阿南德·帕拉库尔 | 天然化合物的三分子复合物 |
CN105999290B (zh) * | 2016-04-21 | 2019-04-09 | 中国人民解放军第四军医大学 | 一种磷脂酰丝氨酸修饰的姜黄素纳米粒 |
WO2018003857A1 (ja) * | 2016-06-29 | 2018-01-04 | 株式会社セラバイオファーマ | 非経口投与用医薬組成物 |
US20170172921A1 (en) * | 2016-12-14 | 2017-06-22 | Mahmoud Reza Jaafari | Polyphenolic compounds encapsualated in long circulating liposomes and use thereof |
KR101948407B1 (ko) | 2017-01-20 | 2019-02-14 | 가천대학교 산학협력단 | 커큐민이 포집된 진세노사이드 및 인지질 기반 지질나노입자를 유효성분으로 함유하는 헬리코박터 파이로리 감염의 예방 또는 치료용 조성물 |
CN107213467A (zh) * | 2017-05-22 | 2017-09-29 | 江苏大学 | 一种姜黄素磷脂复合物的制备方法 |
RU2684111C1 (ru) * | 2018-02-07 | 2019-04-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Южно-Уральский государственный медицинский университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО ЮУГМУ Минздрава России) | Способ получения лекарственного средства с метионином и экстрактом куркумы в виде гранул с кишечнорастворимым покрытием системного действия |
BE1026393B1 (fr) * | 2018-06-18 | 2020-01-28 | Normaphar | Composition pour utilisation dans le traitement de l'ostéopénie et/ou de l'ostéoporose |
FR3082425B1 (fr) * | 2018-06-18 | 2020-09-11 | Normaphar | Composition pour utilisation dans le traitement de l'osteopenie et / ou de l'osteoporose |
CN109846865B (zh) * | 2018-12-26 | 2022-03-25 | 晨光生物科技集团股份有限公司 | 一种姜黄素制剂及其制备方法 |
CN109589410B (zh) * | 2018-12-26 | 2022-02-01 | 晨光生物科技集团股份有限公司 | 一种姜黄素制剂及其制备方法 |
IT201900003907A1 (it) | 2019-03-18 | 2020-09-18 | Indena Spa | Composizioni comprendenti curcumina e coenzima q10 |
CN111803632B (zh) | 2019-04-09 | 2022-04-29 | 北京五和博澳药业股份有限公司 | 黄酮多酚类药物自乳化组合物、其制备方法、药物组合物及用途 |
GB202011069D0 (en) | 2020-07-17 | 2020-09-02 | Univ Of Lincoln | New curcumin products and uses |
KR20220086467A (ko) | 2020-12-16 | 2022-06-23 | 가톨릭대학교 산학협력단 | 다당류를 이용하여 커큐민의 안정성 및 생체 이용률이 향상된 나노복합체 및 이의 제조방법 |
KR20220086018A (ko) | 2020-12-16 | 2022-06-23 | 가톨릭대학교 산학협력단 | 셀룰로오스를 이용하여 커큐민의 안정성 및 생체 이용률이 향상된 나노복합체 및 이의 제조방법 |
EP4289287A1 (en) | 2021-09-28 | 2023-12-13 | Binotec Co., Ltd. | Curcumin nanoparticle complex having modified particle surface and method for preparing same |
JP7321229B2 (ja) * | 2021-10-20 | 2023-08-04 | 義美食品股▲ふん▼有限公司 | ウコン根茎からクルクミノイドを分離する方法 |
CN114557965B (zh) * | 2022-02-09 | 2023-06-09 | 汕头大学 | 一种提高姜黄素稳定性和生物可及性的磷脂复合物纳米粒及制备方法 |
WO2024032507A1 (zh) * | 2022-08-09 | 2024-02-15 | 湖南健瑞医药科技有限公司 | 金属-磷脂复合物、金属-磷脂复合物颗粒和药物-脂质颗粒及其制备方法与应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1657040A (zh) | 2004-11-22 | 2005-08-24 | 山东大学 | 姜黄素磷脂复合物及其制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1215291B (it) | 1985-07-17 | 1990-01-31 | Inverni Della Beffa Spa | Complessi di flavanolignani con fosfolipidi, loro preparazione e relative composizioni farmaceutiche. |
IT1201149B (it) | 1987-01-14 | 1989-01-27 | Indena Spa | Complessi di bioflavonoidi con fosfolipidi,loro preparazione,uso e composizioni farmaceutici e cosmetiche |
IT1203515B (it) | 1987-02-26 | 1989-02-15 | Indena Spa | Complessi di saponine con fosfolipidi e composizioni farmaceutiche e cosmetiche che li contengono |
IT1296920B1 (it) | 1997-12-04 | 1999-08-03 | Indena Spa | Uso di complessi di estratti vitis vinifera con fosfolipidi come agenti anti-aterosclerotici |
IT1304183B1 (it) | 1998-12-18 | 2001-03-08 | Indena Spa | Complessi di proantocianidina a2 con fosfolipidi come agentiantiaterosclerotici. |
CA2536738A1 (en) * | 2003-08-26 | 2005-03-10 | Research Development Foundation | Aerosol delivery of curcumin |
-
2006
- 2006-03-09 EP EP06004820A patent/EP1837030A1/en not_active Withdrawn
-
2007
- 2007-02-21 JP JP2008557619A patent/JP5448462B2/ja active Active
- 2007-02-21 EP EP07703532.7A patent/EP1991244B1/en active Active
- 2007-02-21 SI SI200732132T patent/SI1991244T1/sl unknown
- 2007-02-21 CA CA2644017A patent/CA2644017C/en active Active
- 2007-02-21 HU HUE07703532A patent/HUE046597T2/hu unknown
- 2007-02-21 CN CNA2007800082936A patent/CN101400360A/zh active Pending
- 2007-02-21 PT PT77035327T patent/PT1991244T/pt unknown
- 2007-02-21 ES ES07703532T patent/ES2757580T3/es active Active
- 2007-02-21 WO PCT/EP2007/001487 patent/WO2007101551A2/en active Application Filing
- 2007-02-21 US US12/281,994 patent/US10603329B2/en active Active
- 2007-02-21 PL PL07703532T patent/PL1991244T3/pl unknown
- 2007-02-21 RU RU2008136189/15A patent/RU2450818C2/ru active
- 2007-02-21 KR KR1020087021905A patent/KR101423269B1/ko active IP Right Grant
- 2007-02-21 DK DK07703532T patent/DK1991244T3/da active
- 2007-02-21 AU AU2007222667A patent/AU2007222667B2/en active Active
-
2008
- 2008-09-08 NO NO20083850A patent/NO344242B1/no unknown
- 2008-09-08 IL IL193966A patent/IL193966A/en active IP Right Grant
-
2019
- 2019-02-13 US US16/274,623 patent/US20190175628A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1657040A (zh) | 2004-11-22 | 2005-08-24 | 山东大学 | 姜黄素磷脂复合物及其制备方法 |
Non-Patent Citations (2)
Title |
---|
Began et al.. "Interaction of Curcumin with Phosphatidylcholine: A Spectrofluorometric Study", J Agri Food Chem 47:4992-97 (1999). |
Liu et al., "Validated LC/MS/MS Assay for Curcumin and Tetrahydrocurcumin in Rat Plasma and Application to Pharmacokinetic Study of Phospholipid Complex of Curcumin", J Pharm Biol Anal 40:720-27 (2006). |
Also Published As
Publication number | Publication date |
---|---|
WO2007101551A2 (en) | 2007-09-13 |
EP1837030A1 (en) | 2007-09-26 |
IL193966A (en) | 2015-01-29 |
IL193966A0 (en) | 2011-08-01 |
WO2007101551A3 (en) | 2007-10-25 |
PL1991244T3 (pl) | 2020-03-31 |
KR20080112224A (ko) | 2008-12-24 |
KR101423269B1 (ko) | 2014-07-25 |
ES2757580T3 (es) | 2020-04-29 |
US20090131373A1 (en) | 2009-05-21 |
JP5448462B2 (ja) | 2014-03-19 |
EP1991244B1 (en) | 2019-10-02 |
US20190175628A1 (en) | 2019-06-13 |
CA2644017C (en) | 2019-07-30 |
SI1991244T1 (sl) | 2019-11-29 |
RU2008136189A (ru) | 2010-03-20 |
NO20083850L (no) | 2008-12-03 |
DK1991244T3 (da) | 2019-11-18 |
HUE046597T2 (hu) | 2020-03-30 |
EP1991244A2 (en) | 2008-11-19 |
NO344242B1 (no) | 2019-10-14 |
PT1991244T (pt) | 2019-11-29 |
AU2007222667A1 (en) | 2007-09-13 |
JP2009529506A (ja) | 2009-08-20 |
RU2450818C2 (ru) | 2012-05-20 |
AU2007222667B2 (en) | 2012-11-08 |
CA2644017A1 (en) | 2007-09-13 |
CN101400360A (zh) | 2009-04-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10603329B2 (en) | Phospholipid complexes of curcumin having improved bioavailability | |
US10512616B2 (en) | Composition to enhance the bioavailability of curcumin | |
US10485843B2 (en) | Composition to enhance the bioavailability of curcumin | |
JP2009529506A5 (no) | ||
EP2004206B1 (en) | Phospholipid complexes of olive fruits extracts having improved bioavailability | |
CN113573722A (zh) | 包含姜黄素和辅酶q10的组合物 | |
AU2017239585B2 (en) | Curcuminoid compositions and preparation methods |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: INDENA S.P.A., ITALY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:GIORI, ANDREA;FRANCESCHI, FEDERICO;REEL/FRAME:021961/0501 Effective date: 20080915 |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: FINAL REJECTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NOTICE OF ALLOWANCE MAILED -- APPLICATION RECEIVED IN OFFICE OF PUBLICATIONS |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: PUBLICATIONS -- ISSUE FEE PAYMENT RECEIVED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: PUBLICATIONS -- ISSUE FEE PAYMENT VERIFIED |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 4 |